全部 标题 作者
关键词 摘要

OALib Journal期刊
ISSN: 2333-9721
费用:99美元

查看量下载量

相关文章

更多...

The Food Additive Polyglycerol Polyricinoleate (E-476): Structure, Applications, and Production Methods

DOI: 10.1155/2013/124767

Full-Text   Cite this paper   Add to My Lib

Abstract:

The food additive named polyglycerol polyricinoleate (PGPR) and identified with the code E-476 (PGPR) is used as emulsifier in tin-greasing emulsions for the baking trade and for the production of low-fat spreads. However, the main application of PGPR is in the chocolate industry, where, besides its action as an emulsifier, it also has important properties as a viscosity modifier and thus improves the moulding properties of the molten chocolate. An additional property of PGPR in chocolate is its ability to limit fat bloom. Known chemical methods for preparing this emulsifier involve long reaction times and high operating temperatures, which adversely affect the quality of the final product leading to problems of coloration and odors that could make it inadvisable for the food industry. As an alternative, the enzymatic synthesis of PGPR by the catalytic action of two lipases has been developed. The enzymes act in mild reaction conditions of temperature and pressure, neutral pH, and in a solvent-free system, which makes the process environmentally friendly and avoids side reaction, so that the product has a higher purity and quality. 1. Food Additives Food additives have been developed over the years to meet the needs of food production, as making foods on a large scale is a very different task to making them in the kitchen at home. Additives are needed to ensure processed food remains in a good condition throughout its journey from the factory to the shop and to the consumer at home. Some are so essential that they are even used in organic foods [1–3]. In the broadest of terms, food additives are substances intentionally added to food either directly or indirectly with one or more of the following purposes [4]:(1)to maintain or improve nutritional quality;(2)to maintain product quality and freshness;(3)to aid in the processing or preparation of food;(4)to make food more appealing. On the other hand, food additives may only be authorized if [4](1)there is a technological need for their use;(2)they do not mislead the consumer;(3)they present no hazard to the health of the consumer. The use of food additives must always be labelled on the packaging of food products by their category (antioxidant, preservative, colour, etc.) with either their name or E number. In the United States, food additives are regulated by the Food and Drug Administration. Two sections of the regulations govern their use: substances affirmed as GRAS, that is, Generally Recognized as Safe, (21CFR184) and Direct Food Additives (21CFR172). Substances that have been affirmed as GRAS

References

[1]  R. MacRae, R. K. Robinson, and M. J. Sadler, Eds., Encyclopaedia of Food Science, Food Technology, and Nutrition, vol. 8, Academic Press, New York, NY, USA, 1993.
[2]  Y. H. Hui, Ed., Encyclopedia of Food Science and Technology, vol. 4, John Wiley & Sons, New York, NY, USA, 1992.
[3]  P. J. Fellows, Food Processing Technology: Principles and Practices, Woodhead Publishing Limited, Cambridge, UK, 3rd edition, 2009.
[4]  A. L. Branen, P. M. Davidson, S. Salminen, and J. Thorngate, Eds., Food Additives, Taylor & Francis, Boca Raton, Fla, USA, 2001.
[5]  T. E. Furia, Ed., Handbook of Food Additives, vol. 2, CRC Press, New York, NY, USA, 2nd edition, 1980.
[6]  J. A. Maga and A. T. Tu, Eds., Food Additive Toxicology, Taylor & Francis, London, UK, 1995.
[7]  J. S. Smith, Ed., Food Additive User's Handbook, Springer, New York, NY, USA, 1991.
[8]  Codex alimentarius, 2012, http://www.codexalimentarius.org.
[9]  H. Moonen and H. Bas ", “Mono- and diglycerides,” in Emulsifiers in Food Technology, R. J. Whitehurst, Ed., John Wiley & Sons, New York, NY, USA, 2008.
[10]  NPCS Board of Consultants & Engineers, The Complete Book on Emulsifiers With Uses, Formulae and Processes, 2007.
[11]  G. L. Hasenhuettl and R. W. Hartel, Eds., Emulsifiers and Their Applications, Springer, New York, NY, USA, 2008.
[12]  C. Stauffer, Emulsifiers, Eagan Press, 1999.
[13]  N. Garti, “Food emulsifiers. structure-reactivity relationships, design, and applications,” in Physical Properties of Lipids, A. G. Marangoni and S. S. Narine, Eds., Taylor & Francis, London, UK, 2002.
[14]  C. C. Cai, “Emulsifiers used in food applications, focusing on the meat processing industry,” Palsgaard Technical Paper, 2011.
[15]  C. E. Stauffer, “Emulsifiers for the food industry,” in Bailey’a Induatrial Oil and Fat Producta, F. Shahidi, Ed., John Wiley & Sons, New York, NY, USA, 2005.
[16]  M. Gómez, S. Del Real, C. M. Rosell, F. Ronda, C. A. Blanco, and P. A. Caballero, “Functionality of different emulsifiers on the performance of breadmaking and wheat bread quality,” European Food Research and Technology, vol. 219, no. 2, pp. 145–150, 2004.
[17]  L. Stampfli and B. Nersten, “Emulsifiers in bread making,” Food Chemistry, vol. 52, pp. 353–360, 1995.
[18]  Z. Kohajdová, J. Karovi?ová, and ?. Schmidt , “Significance of emulsifiers and hydrocolloids in bakery industry,” Acta Chimica Slovaca, vol. 2, pp. 46–461, 2009.
[19]  R. T. McIntyre, “Polyglycerol esters,” Journal of the American Oil Chemists' Society, vol. 56, pp. A835–A840, 1979.
[20]  M. F. Stewart and E. J. Hughes, “Polyglycerol esters as food additives,” Process Biochemistry Journal, vol. 7, pp. 27–28, 1972.
[21]  N. Garti, G. F. Remon, and B. Zaidman, “Polyglycerol esters of vegetable oils,” Tenside, Surfactants, Detergents, vol. 23, no. 6, pp. 320–324, 1986.
[22]  N. Garti, A. Aserin, and B. Zaidman, “Polyglycerol esters: optimization and techno-economic evaluation,” Journal of the American Oil Chemists' Society, vol. 58, no. 9, pp. 878–883, 1981.
[23]  “Polyglycerols in food applications,” Application data sheet. Solvay Chemicals International.
[24]  J. Holstborg, B. V. Pedersen, N. Krog, and S. K. Olesen, “Physical properties of diglycerol esters in relation to rheology and stability of protein-stabilised emulsions,” Colloids and Surfaces B, vol. 12, no. 3–6, pp. 383–390, 1999.
[25]  S. K. Olesen and N. Krog, “Phase behaviour of new food emulsifiers and their application,” in Oils and Fats in Food Applications: Proceedings of the Food Applications Session of the 22nd Congress of the International Society of Fats Research (ISF), Kuala Lumpur, Malaysia, 7–12 September 1997, K. G. Berger, Ed., 1997.
[26]  A. Sein, J. A. Verheij, and W. G. M. Agterof, “Rheological characterization, crystallization, and gelation behavior of monoglyceride gels,” Journal of Colloid and Interface Science, vol. 249, no. 2, pp. 412–422, 2002.
[27]  N. Krog, “Crystallization properties and lyotropic phase behavior of food emulsifiers,” in Crystallization Processes in Fats and Lipid Systems, N. Garti and K. Sato, Eds., Taylor & Francis, London, UK, 2001.
[28]  P. Seiden and J. B. Martin, “Process for preparing polyglycerol,” US 3,968,169, 1976.
[29]  “Polyglycerols—general overview,” Product data sheet. Solvay Chemical International.
[30]  V. Norn, “Polyglycerol esters,” in Emulsifiers in Food Technology, R. J. Whitehurst, Ed., 2008.
[31]  T. Ushikusa, T. Maruyama, I. Nhya, and M. Okada, “Pyrolysis behaviors and thermostability of polyglycerols and polyglycerol fatty acid esters,” Journal of the Japan Oil Chemists' Society, vol. 39, no. 5, pp. 314–320, 1990.
[32]  “Polyglycerols for ester production,” Application data sheet. Solvay Chemical International.
[33]  F. van de Velde, F. Weinbreck, M. W. Edelman, E. Van Der Linden, and R. H. Tromp, “Visualisation of biopolymer mixtures using confocal scanning laser microscopy (CSLM) and covalent labelling techniques,” Colloids and Surfaces B, vol. 31, no. 1–4, pp. 159–168, 2003.
[34]  I. Kobayashi, X. Lou, S. Mukataka, and M. Nakajima, “Preparation of monodisperse water-in-oil-in-water emulsions using microfluidization and straight-through microchannel emulsification,” Journal of the American Oil Chemists' Society, vol. 82, no. 1, pp. 65–71, 2005.
[35]  J. Su, J. Flanagan, Y. Hemar, and H. Singh, “Synergistic effects of polyglycerol ester of polyricinoleic acid and sodium caseinate on the stabilisation of water-oil-water emulsions,” Food Hydrocolloids, vol. 20, no. 2-3, pp. 261–268, 2006.
[36]  J. Surh, G. T. Vladisavljevi?, S. Mun, and D. J. McClements, “Preparation and characterization of water/oil and water/oil/water emulsions containing biopolymer-gelled water droplets,” Journal of Agricultural and Food Chemistry, vol. 55, no. 1, pp. 175–184, 2007.
[37]  A. Benichou, A. Aserin, and N. Garti, “Polyols, high pressure, and refractive indices equalization for improved stability of W/O emulsions for food applications,” Journal of Dispersion Science and Technology, vol. 22, no. 2-3, pp. 269–280, 2001.
[38]  S. Mun, Y. Choi, S. J. Rho, C. G. Kang, C. H. Park, and Y. R. Kim, “Preparation and characterization of water/oil/water emulsions stabilized by polyglycerol polyricinoleate and whey protein isolate,” Journal of Food Science, vol. 75, no. 2, pp. E116–E125, 2010.
[39]  D. Sa?lam, P. Venema, R. de Vries, L. M. C. Sagis, and E. van der Linden, “Preparation of high protein micro-particles using two-step emulsification,” Food Hydrocolloids, vol. 25, no. 5, pp. 1139–1148, 2011.
[40]  R. Wilson, B. J. van Schie, and D. Howes, “Overview of the preparation, use and biological studies on polyglycerol polyricinoleate (PGPR),” Food and Chemical Toxicology, vol. 36, no. 9-10, pp. 711–718, 1998.
[41]  E. Flack, “Margarines and spreads,” in Food Emulsifiers and Their Applications, G. L. Hasenhuettl and R. W. Hartel, Eds., Springer, New York, NY, USA, 1997.
[42]  S. M. Clegg, A. K. Moore, and S. A. Jones, “Low-fat margarine spreads as affected by aqueous phase hydrocolloids,” Journal of Food Science, vol. 61, no. 5, pp. 1073–1079, 1996.
[43]  B. Schantz and H. Rohm, “Influence of lecithin-PGPR blends on the rheological properties of chocolate,” Lebensm-wiss u-Technol, vol. 38, no. 1, pp. 41–45, 2005.
[44]  H. F. Banford, K. J. Gardiner, G. R. Howat, and A. F. Thomson, “The use of polyglycerol polyricinoleate in chocolate,” Confectionery Production, vol. 36, pp. 359–365, 1970.
[45]  P. Lonchampt and R. W. Hartel, “Fat bloom in chocolate and compound coatings,” European Journal of Lipid Science and Technology, vol. 106, pp. 241–274, 2004.
[46]  R. Peschar, M. M. Pop, D. J. A. de Ridder, J. B. van Mechelen, R. A. J. Driessen, and H. Schenk, “Crystal structures of 1,3-distearoyl-2-oleoylglycerol and cocoa butter in the β(V) phase reveal the driving force behind the occurrence of fat bloom on chocolate,” Journal of Physical Chemistry B, vol. 108, no. 40, pp. 15450–15453, 2004.
[47]  H. Schenk and R. Peschar, “Understanding the structure of chocolate,” Radiation Physics and Chemistry, vol. 71, pp. 829–835, 2004.
[48]  R. Wilson and M. Smith, “A three-generation reproduction study on polyglycerol polyricinoleate (PGPR) in wistar rats,” Food and Chemical Toxicology, vol. 36, no. 9-10, pp. 739–741, 1998.
[49]  R. Wilson and M. Smith, “Human studies on polyglycerol polyricinoleate (PGPR),” Food and Chemical Toxicology, vol. 36, no. 9-10, pp. 743–745, 1998.
[50]  R. Wilson, B. H. Doell, W. Groger, J. Hope, and J. B. M. Gellatly, “The physiology of liver enlargement,” in Metabolic Aspects of Food Safety, F. J. C. Roe, Ed., 1970.
[51]  D. Howes, R. Wilson, and C. T. James, “The fate of ingested glyceran esters of condensed castor oil fatty acids [polyglycerol polyricinoleate (PGPR)] in the rat,” Food and Chemical Toxicology, vol. 36, no. 9-10, pp. 719–738, 1998.
[52]  J. Philp McL, “Evaluation of the safety of foods,” Proceedings of the Nutrition Society, vol. 40, pp. 47–56, 1981.
[53]  JECFA, “17th Report on the Joint FAO/WHO Expert Committee on Food Additives,” 1973, http://www.fao.org/.
[54]  “Report from the Commission on Dietary Food Additive Intake in the European Union,” Commission of the European Communities, Brussels, Belgium, 2001.
[55]  Directive No 95/2/EC of the European Parliament and of the Council of 20 February 1995 on food additives other than colours and sweeteners.
[56]  Commission Directive 2008/84/EC of the European Parliament and of the Council of 27 August 2008 laying down specific purity criteria on food additives other than colours and sweeteners.
[57]  P. Denecke, G. B?rner, and V. V. Allmen, “Method of preparing polyglycerol polyricinoleic fatty acid esters,” GB2073232A, 1981.
[58]  S. N. Modak and J. G. Kane, “Studies in estolides. I. Kinetics of estolide formation and decomposition,” Journal of the American Oil Chemists' Society, vol. 42, pp. 428–232, 1965.
[59]  K. T. Achaya, “Chemical derivatives of castor oil,” Journal of the American Oil Chemists' Society, vol. 48, no. 11, pp. 758–763, 1971.
[60]  R. Tenore, “Process for the direct manufacture of polyglycerol polyricinoleate,” WO 2007/027447 A1, 2007.
[61]  A. Manresa, A. Bódalo, J. L. Gómez et al., “Method for obtaining polyglycerol polyricinoleate,” WO 2088/031908 A1, 2008.
[62]  A. Bódalo, J. Bastida, M. F. Máximo, M. C. Montiel, and M. D. Murcia, “Enzymatic biosynthesis of ricinoleic acid estolides,” Biochemical Engineering Journal, vol. 26, pp. 155–158, 2005.
[63]  A. Bódalo, J. Bastida, M. F. Máximo, M. C. Montiel, M. Gómez, and M. D. Murcia, “Production of ricinoleic acid estolide with free and immobilised lipase from Candida rugosa,” Biochemical Engineering Journal, vol. 39, pp. 450–456, 2008.
[64]  A. Bódalo, J. Bastida, M. F. Máximo, M. C. Montiel, M. D. Murcia, and S. Ortega, “Influence of the operating conditions on lipase-catalysed synthesis of ricinoleic acid estolides in solvent-free systems,” Biochemical Engineering Journal, vol. 44, no. 2-3, pp. 214–219, 2009.
[65]  A. Bódalo, J. Bastida, M. F. Máximo, M. C. Montiel, M. Gómez, and S. Ortega, “Screening and selection of lipases for the enzymatic production of polyglycerol polyricinoleate,” Biochemical Engineering Journal, vol. 46, pp. 217–222, 2009.
[66]  J. L. Gómez, J. Bastida, M. F. Máximo, M. C. Montiel, M. D. Murcia, and S. Ortega, “Solvent-free polyglycerol polyricinoleate synthesis mediated by lipase from Rhizopus arrhizus,” Biochemical Engineering Journal, vol. 54, pp. 111–116, 2011.
[67]  N. N. Gandhi, “Applications of lipase,” Journal of the American Oil Chemists' Society, vol. 74, pp. 621–634, 1997.
[68]  D. G. Hayes and R. Kleiman, “Lipase-catalyzed synthesis and properties of estolides and their esters,” Journal of the American Oil Chemists' Society, vol. 72, no. 11, pp. 1309–1316, 1995.
[69]  D. G. Hayes, “The catalytic activity of lipases toward hydroxyl fatty acids. A review,” Journal of the American Oil Chemists' Society, vol. 73, pp. 543–549, 1996.
[70]  F. Ergan, M. Trani, and G. André, “Production of glycerides from glycerol and fatty acid by immobilized lipases in non-aqueous media,” Biotechnology and Bioengineering, vol. 35, no. 2, pp. 195–200, 1990.
[71]  D. Charlemagne and M. D. Legoy, “Enzymatic synthesis of polyglycerol-fatty acid esters in solvent-free system,” Journal of the American Oil Chemists' Society, vol. 72, pp. 61–65, 1995.
[72]  G. W. V. Cave, C. L. Raston, and J. L. Scott, “Recent advances in solventless organic reactions: towards benign synthesis with remarkable versatility,” Chemical Communications, no. 21, pp. 2159–2169, 2001.
[73]  G. Hills, “Industrial use of lipases to product fatty acid esters,” European Journal of Lipid Science and Technology, vol. 105, pp. 601–607, 2003.
[74]  P. T. Anastas and J. C. Warner, Green Chemistry: Theory and Practice, Oxford University Press, New York, NY, USA, 1998.
[75]  C. Yamaguchi, M. Akita, S. Asaoka, and F. Osada, “Enzymatic manufacture of castor oil fatty acid estolides,” JP 8916591, 1988.
[76]  C. Yamaguchi, A. Tooyama, S. Asaoka, and F. Osada, “Manufacture of glycerin-free estolides from castor oil with lipase,” JP 9013387, 1989.
[77]  C. Yamaguchi, et al., “Production of estolide,” JP 5211878, 1993.
[78]  Y. Yoshida, et al., “Production of estolide from ricinoleic acid,” JP 5304966, 1993.
[79]  Y. Yoshida, M. Kawase, C. Yamaguchi, and T. Yamane, “Enzymatic synthesis of estolides by a bioreactor,” Journal of the American Oil Chemists' Society, vol. 74, no. 3, pp. 261–267, 1997.
[80]  Y. Yoshida, M. Kawase, C. Yamaguchi, and T. Yamane, “Synthesis of estolides with immobilized lipase,” Yukagaku, vol. 44, pp. 328–333, 1995.
[81]  A. Bódalo, E. Gómez, J. L. Gómez, J. Bastida, M. F. Máximo, and F. Díaz, “A comparison of different methods of β-galactosidase immobilization,” Process Biochemistry Journal, vol. 26, pp. 349–353, 1991.
[82]  J. L. Gómez, A. Bódalo, E. Gómez, J. Bastida, A. M. Hidalgo, and M. Gómez, “Immobilisation of peroxidase on glass beads: an improved alternative for phenol removal,” Enzyme and Microbial Technology, vol. 39, pp. 2016–2022, 2006.
[83]  E. F. Hartree, “Protein determination and improved modification of the Lowry’s method which gives a linear photometric response,” Analytical Biochemistry, vol. 42, pp. 422–427, 1973.
[84]  ASTM D974-06, “Standard test method for acid and base number by color indicator titration”.
[85]  J. C. Santos, G. F. M. Nunes, A. B. R. Moreira, V. H. Perez, and H. F. de Castro, “Characterization of Candida rugosa lipase immobilized on poly(N-methylolacrylamide) and its application in butyl butyrate synthesis,” Chemical Engineering and Technology, vol. 30, no. 9, pp. 1255–1261, 2007.
[86]  L. Guo, Z. Zhang, Y. Zhu, J. Li, and Z. Xie, “Synthesis of polysiloxane-polyester copolymer by lipase-catalyzed polycondensation,” Journal of Applied Polymer Science, vol. 108, no. 3, pp. 1901–1907, 2008.
[87]  H. T. Dang, O. Obiri, and D. G. Hayes, “Feed batch addition of saccharide during saccharide-fatty acid esterification catalyzed by immobilized lipase: time course, water activity, and kinetic model,” Journal of the American Oil Chemists' Society, vol. 82, no. 7, pp. 487–493, 2005.
[88]  M. Goldberg, D. Thomas, and M. D. Legoy, “The control of lipase-catalysed transesterification and esterification reaction rates. Effects of substrate polarity, water activity and water molecules on enzyme activity,” European Journal of Biochemistry, vol. 190, no. 3, pp. 603–609, 1990.
[89]  A. R. M. Yahya, W. A. Anderson, and M. Moo-Young, “Ester synthesis in lipase catalysed reactions,” Enzyme and Microbial Technology, vol. 23, pp. 438–450, 1998.
[90]  A. M. Klibanov, “Enzymatic catalysis in anhydrous organic solvents,” Trends in Biochemical Sciences, vol. 14, no. 4, pp. 141–144, 1989.
[91]  “Sigma Aldrich catalog,” En, http://www.sigmaaldrich.com/.
[92]  Y. Yesiloglu, “Utilization of bentonite as a support material for immobilisation of Candida rugosa lipase,” Process Biochemistry Journal, vol. 40, pp. 2155–2159, 2005.
[93]  Committee on Food Chemicals Codex, Food and Nutrition Board, and Institute of Medicine, Food Chemicals Codex, 5th edition, 2004.
[94]  S. Ortega Requena, Síntesis biocatalítica de polirricinoleato de poliglicerol [Ph.D. thesis], University of Murcia, Murcia, Spain, 2012.

Full-Text

Contact Us

service@oalib.com

QQ:3279437679

WhatsApp +8615387084133